I co-founded a startup in 1996 and sold 51% two years later to an interactive company for notes. After the 2000 crash they could not find more capital so we reversed the transaction and took the company back. They had moved the company to another city, had about 30 employees, $ 2 mm in outstanding debt (and one was the hosting company who was ready to shut it off), and nothing in the bank. Faced with certain failure, I called my original investor to convince him to help recapitalize the company. The worst thing he could have said was "no". If he said no, our position was not materially worse than not asking at all. Any nobody was writing checks those days. So I strapped on, went to see him, and he said yes. By doing this, we saved the company, his original investment, and built a hell of a business we sold 4 years later for a 300% return for him and some left to management and employees. You cannot let your own fear of failure shut you off from thinking strategically.